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All of Hugh Hefner's past and present girlfriends and wives. This long list of lovers and exes covers an entire lifespan yet the women seem to always be young. One of many famous celebs who married much younger womenHugh Hefner has only been married a couple times but he's dated continuously.

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Hefner had no shortage of girlfriends and wives during his tenure as one of the world's most notorious publishers. She went on to appear on four Playboy covers and posed nude in the magazine. The couple met at a party after high school, though Hefner left soon after for the United States Army.

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She regrets her time in the Playboy mansion. Photo: Playboy. Hefner died at 92 on Sept.

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The Playboy cover model and reality star dishes about what really went on in the Playboy Mansion in her book, "Sliding Into Home. At the very least, I would make a couple hundred dollars, meet some cool people, and get a chance to check out the Playboy Mansion. How could I turn that down?

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Playboy founder Hugh Hefner has had countless lovers over the years — some more notable than others. Here's a chronological history of the wives, girlfriends, and Bunnies who found themselves in his bed. Because Hef has never been a one-woman man, there's a lot of overlap.

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The publication recently made headlines by halting nude photography, but they vow to keep the content scintillating in other ways. But what is more iconic about Playboy than the man, the myth, the legend himself: Hugh Hefner. Other than his obvious business prowess, the owner of Playboy Enterprises is known for being just that: a playboy.

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Hugh Hefner born April 9, - September 27, made a cameo appearance as himself in the Season 9 episode of Roseanne titled " What a Day for a Daydream ". Hugh Hefner transformed the adult entertainment industry with his ground breaking publication Playboy magazine. His teachers, however, described him as "unenthusiastic.

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I just got really emotional over [posing with the others for a November '05 pictorial], and I'm embarrassed about it now. Kendra Wilkinson: I have no regrets. Everything I do, I am good with!

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She was so traumatised by life in the house that she developed a stammer. In her biography, Down the Rabbit Hole, the blonde Girls Next Door star described how she first met Hef after scoring an invite to a Playboy party during whilst working as a busty waitress at Hooters in LA. Having moved from Oregon to study at college and make it as an actress, she hoped the invite could at least score her an audition for the magazine.

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